Article ID Journal Published Year Pages File Type
5274028 Tetrahedron Letters 2009 4 Pages PDF
Abstract

The addition of triorganozincates to (R)-N-(tert-butanesulfinyl)benzaldimine has been performed with very good results by using a catalytic amount of Me2Zn (0.15 equiv) to generate the organozincate. Yields and/or diastereoselectivities of the formed α-branched sulfinamides improve in comparison with the values obtained in the same reactions carried out with an excess of a previously formed triorganozincate. On the other hand, the transfer of the two alkyl groups of a dialkylzinc reagent to the imine has been achieved by using 0.5 equiv of dialkylzinc and 1.5 equiv of MeMgBr to generate the trialkylzincate. In both methods, good to excellent yields and diastereomeric ratios (up to 98:2) have been obtained.

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Physical Sciences and Engineering Chemistry Organic Chemistry
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